Shelter Island Vacations from ₩1,498,242

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ₩234,741 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Shelter Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Nova Hotel Brooklyn

Nova Hotel Brooklyn

3 out of 5
Price was ₩2,019,298, price is now ₩1,498,242 per person
₩1,498,242
per person
Jun 4 - Jun 9
found 6 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Newark Liberty Intl. Airport (EWR)
8.4/10 Very Good! (1,117 reviews)
The staff was very welcoming room was very clean and definitely visiting again

Reviewed on Mar 17, 2026

Court Square Hotel Long Island City New York , Belvilla District 6 Formerly Sonder

Court Square Hotel Long Island City New York , Belvilla District 6 Formerly Sonder

3.5 out of 5
Queens
Save 100% on your flight
Price was ₩2,463,122, price is now ₩1,672,250 per person
₩1,672,250
per person
Jun 4 - Jun 9
found 6 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Newark Liberty Intl. Airport (EWR)
8.6/10 Excellent! (201 reviews)
Problems may occur when you booked a hotel without a front desk: 1) basically no in-time reply; 2) when you call the online agent, it will take them quite long to get back to you and sometimes he doesn’t even solve your problem. We arrived before check-in time but we couldn’t use the lockers to store our luggage, while the online agent kept asking us to continue trying and didn’t offer any help😅😅 wasted us almost one hour…. Overall the room is clean, with many kitchen stuff. Remember to bring your own slippers, toothbrush and paste because they didn’t provide. Transportation is very convenient, closed to E/G/F and 7 metro lines. But it also means you can hear sound of line 7 in your room. Think twice if you are a light sleeper. Safe neighborhood.

Reviewed on Mar 22, 2026

The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
Price was ₩11,701,091, price is now ₩8,471,660 per person
₩8,471,660
per person
Apr 27 - May 3
found 1 day ago
Roundtrip flight included
Seoul (ICN) to Newark Liberty Intl. Airport (EWR)
9.6/10 Exceptional! (196 reviews)
Absolutely everything. Amazingly appointed room, very friendly stafff.

Reviewed on Mar 1, 2026

LGA AIRPORT

LGA AIRPORT

2 out of 5
Queens
Save 100% on your flight
Price was ₩3,675,362, price is now ₩2,761,490 per person
₩2,761,490
per person
Jun 4 - Jun 9
found 6 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to New York (JFK)
No reviews

Where to stay in Shelter Island

Find the best Shelter Island areas and neighborhoods for the activities you enjoy most. Learn more about Shelter Island
Center console boat on Long Island, NY. Photographed by drone.

Silver Beach

While Silver Beach might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Sunset Beach and Crescent Beach.

Find hotels in Silver Beach

Find the Best Shelter Island Vacation Packages

Shelter Island Beach Vacation

There's nothing like a Shelter Island vacation to give you a little extra bounce in your step. The sound of rolling surf and the smell of clean ocean air are sure to refresh your mind, body and soul. To be close to the town center on your trip to Shelter Island, find a hotel around Wades Beach (2 kilometers away). If you're planning to stay for a bit, look into our Shelter Island packages. Not only can you save some cash, you'll also have other amazing beaches near you to explore, like Shell Beach and Menhadden Lane Beach.

Shelter Island Hotel Deals

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
The price is ₩575,203 per night from Mar 23 to Mar 24
₩575,203
₩788,602 total
Mar 23 - Mar 24
includes taxes & fees
8.4/10 Very Good! (740 reviews)
The food was delicious. There was an issue with the pool which will be fixed soon. My big complaint was room location. I am a senior citizen and my room was in the 700's. Many steep stairs to get down to main building. They offered a ride from my room to main building which I had to use because it ...

Reviewed on Mar 21, 2026

Gurney's Montauk Resort & Seawater Spa
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
The price is ₩227,375 per night from Mar 23 to Mar 24
₩227,375
₩289,241 total
Mar 23 - Mar 24
includes taxes & fees
9.2/10 Wonderful! (1,306 reviews)
Great property

Reviewed on Mar 19, 2026

Montauk Manor
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
The price is ₩293,882 per night from Mar 23 to Mar 24
₩293,882
₩363,904 total
Mar 23 - Mar 24
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
Easy

Reviewed on Mar 21, 2026

Water's Edge Resort & Spa
See all 4,740 properties in Shelter Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Discover the most popular places to visit in Shelter Island

Havens House

You can spend an afternoon browsing the exhibits at Havens House during your trip to Shelter Island. Stroll along the area's beaches or simply enjoy its wineries.

Havens House

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.